pirenzepine   Click here for help

GtoPdb Ligand ID: 328

Approved drug
pirenzepine is an approved drug
Compound class: Synthetic organic
Comment: Pirenzepine muscarinic acetylcholine receptor antagonist, selective for the M1 receptor subtype.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 74.23
Molecular weight 351.17
XLogP 1.32
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CN1CCN(CC1)CC(=O)n1c2ccccc2c(=O)[nH]c2c1nccc2
Isomeric SMILES CN1CCN(CC1)CC(=O)n1c2ccccc2c(=O)[nH]c2c1nccc2
InChI InChI=1S/C19H21N5O2/c1-22-9-11-23(12-10-22)13-17(25)24-16-7-3-2-5-14(16)19(26)21-15-6-4-8-20-18(15)24/h2-8H,9-13H2,1H3,(H,21,26)
InChI Key RMHMFHUVIITRHF-UHFFFAOYSA-N
References
1. Buckley NJ, Bonner TI, Buckley CM, Brann MR. (1989)
Antagonist binding properties of five cloned muscarinic receptors expressed in CHO-K1 cells.
Mol Pharmacol, 35 (4): 469-76. [PMID:2704370]
2. Carr BJ, Mihara K, Ramachandran R, Saifeddine M, Nathanson NM, Stell WK, Hollenberg MD. (2018)
Myopia-Inhibiting Concentrations of Muscarinic Receptor Antagonists Block Activation of Alpha2A-Adrenoceptors In Vitro.
Invest Ophthalmol Vis Sci, 59 (7): 2778-2791. [PMID:29860464]
3. Dörje F, Wess J, Lambrecht G, Tacke R, Mutschler E, Brann MR. (1991)
Antagonist binding profiles of five cloned human muscarinic receptor subtypes.
J Pharmacol Exp Ther, 256 (2): 727-33. [PMID:1994002]
4. Hegde SS, Choppin A, Bonhaus D, Briaud S, Loeb M, Moy TM, Loury D, Eglen RM. (1997)
Functional role of M2 and M3 muscarinic receptors in the urinary bladder of rats in vitro and in vivo.
Br J Pharmacol, 120 (8): 1409-18. [PMID:9113359]
5. Huang F, Buchwald P, Browne CE, Farag HH, Wu WM, Ji F, Hochhaus G, Bodor N. (2001)
Receptor binding studies of soft anticholinergic agents.
AAPS PharmSci, 3 (4): E30. [PMID:12049493]
6. Jolkkonen M, van Giersbergen PL, Hellman U, Wernstedt C, Karlsson E. (1994)
A toxin from the green mamba Dendroaspis angusticeps: amino acid sequence and selectivity for muscarinic m4 receptors.
FEBS Lett, 352 (1): 91-4. [PMID:7925952]
7. Kashihara K, Varga EV, Waite SL, Roeske WR, Yamamura HI. (1992)
Cloning of the rat M3, M4 and M5 muscarinic acetylcholine receptor genes by the polymerase chain reaction (PCR) and the pharmacological characterization of the expressed genes.
Life Sci, 51 (12): 955-71. [PMID:1325587]
8. Kovacs I, Yamamura HI, Waite SL, Varga EV, Roeske WR. (1998)
Pharmacological comparison of the cloned human and rat M2 muscarinic receptor genes expressed in the murine fibroblast (B82) cell line.
J Pharmacol Exp Ther, 284 (2): 500-7. [PMID:9454790]
9. Nelson CP, Nahorski SR, Challiss RA. (2006)
Constitutive activity and inverse agonism at the M2 muscarinic acetylcholine receptor.
J Pharmacol Exp Ther, 316 (1): 279-88. [PMID:16188951]
10. Stein R, Pinkas-Kramarski R, Sokolovsky M. (1988)
Cloned M1 muscarinic receptors mediate both adenylate cyclase inhibition and phosphoinositide turnover.
EMBO J, 7 (10): 3031-5. [PMID:2846274]
11. Wess J, Lambrecht G, Mutschler E, Brann MR, Dörje F. (1991)
Selectivity profile of the novel muscarinic antagonist UH-AH 37 determined by the use of cloned receptors and isolated tissue preparations.
Br J Pharmacol, 102 (1): 246-50. [PMID:2043926]